Acetic Anhydride → 2H-1-Benzopyran-6-ol, 3,4-dihydro-, 6-acetate

HRID 637730Notes

Reaction equation

HRID 637730 reaction equation
COC1[C:4](C=O)=[CH:5][C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2C=1.[C:15]([O:18][C:19](=[O:21])[CH3:20])(=O)[CH3:16]>N1C=CC=CC=1>[C:19]([O:18][C:15]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:16]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10352557HCID 10352557, compound

Product 1

HCID 184148222H-1-Benzopyran-6-ol, 3,4-dihydro-, 6-acetateYield 108.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-methoxy-3,4-dihydrobenzopyran-7-carboxaldehyde (5.00 g, 28.1 mmol) in pyridine (15.0 mL) was added acetic anhydride (3.5 mL, 31.1 mmol) and the mixture allowed to stir at room temperature for 4 hours then poured into ice water (300 mL). The product which precipitated was collected by filtration, washed with water (75 mL) and air dried to afford 6-acetoxy-3,4-dihydrobenzopyran, (5.86 gm, 94.5%), m.p. 76°-77°.

Workup

  1. customThe product which precipitated
  2. filtrationwas collected by filtration
  3. washwashed with water (75 mL) and air
  4. customdried

Sources & evidence

ORD record
ord-7528ee70ab4e4937a15cd5a3e9a9ce01
Source dataset
uspto-grants-1985_12
Patent number
US04558067

Reaction notes

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