Acetic Anhydride → HCID 4982652, compound

HRID 638152Notes

Reaction equation

HRID 638152 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:4]=2[O:3]1.[OH-].[Na+].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[C:15]([O:11][C:10]1[C:4]2[O:3][C:2]([CH3:12])([CH3:1])[CH2:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranol

Product 1

HCID 4982652HCID 4982652, compoundYield 94.6%

Procedure

2,3-Dihydro-2,2-dimethyl-7-benzofuranol (16.4 g, 0.1 mol) was dissolved in 100 ml of an aqueous solution of sodium hydroxide (6.0 g, 0.15 mol), and 12.8 g of acetic anhydride was dumped into the solution and thoroughly mixed, whereby a white solid substance was precipitated. This substance was collected by filtration and dried, whereby 19.5 g of 7-acetoxy-2,3-dihydro-2,2-dimethylbenzofuran was obtained. The melting point of this product was 48.5°-49.5° C. This phenol acetate was dissolved in 400 ml of chloroform, and 60 ml of 70% nitric acid was dropwise added at -5° C. Then, the stirring was continued at 10° C. for one hour. The reaction solution was washed with water, then dried over anhydrous sodium sulfate and concentrated. The solid substance thereby obtained was recrystallized from benzene-cyclohexane, whereby 19.6 g of 7-acetoxy-2,3-dihydro-2,2-dimethyl-5-nitrobenzofuran was obtained. The melting point of this product was 141°-142° C. The structure was confirmed by 1H-NMR spectrum and IR spectrum. Then, the product was added to a solution containing 35 g of sodium hydroxide in 200 ml of water and 50 ml of methanol, and heated at 40° C. for 15 minutes to complete hydrolysis. The reaction solution was neutralized by concentrated hydrochloric acid, and then extracted with ether. The extracted solution was washed with water, then dried over anhydrous sodium sulfate and concentrated, whereby 13.0 g of substantially pure 2,3-dihydro-2,2-dimethyl-5-nitro-7-benzofuranol was obtained. The melting point of this product was 97°-97.5° C. The phenol thus obtained, was reacted with O-ethyl-S-n-propyl-thiophosphoryl chloride in the same manner as in Example 1, whereby the compound (No. 4) identified in Table 1 was obtained as oily substance.

Workup

  1. additionthoroughly mixed
  2. customwhereby a white solid substance was precipitated
  3. filtrationThis substance was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-be5e38aed0e046bbaaf43aec7995e91a
Source dataset
uspto-grants-1985_12
Patent number
US04560682

Reaction notes

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