Water → 2-Chloroacetoxy-5-cyano-2,3-dihydro-3,3-dimethylbenzofuran

HRID 444088Notes

Reaction equation

HRID 444088 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH:14]([OH:16])[C:13]([CH3:18])([CH3:17])[C:12]=2[CH:19]=1)#[N:7].C(N(CC)CC)C.O>C(OCC)C>[Cl:1][CH2:2][C:3]([O:16][CH:14]1[C:13]([CH3:17])([CH3:18])[C:12]2[CH:19]=[C:8]([C:6]#[N:7])[CH:9]=[CH:10][C:11]=2[O:15]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 205362002-Hydroxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-carbonitrile

Product 1

HCID 537643532-Chloroacetoxy-5-cyano-2,3-dihydro-3,3-dimethylbenzofuranYield 34.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloroacetyl chloride (3.6 g) was added dropwise to a solution of 5-cyano-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (5 g) prepared as in Example 10, and triethylamine (3.2 g) in diethyl ether (50 ml) with stirring and cooling. After 3 hours at room temperature, the mixture was shaken with water and an insoluble solid product was filtered off and dried to give 2.4 g of title compound, mp 138° C.

Workup

  1. temperaturecooling
  2. filtrationan insoluble solid product was filtered off
  3. customdried

Sources & evidence

ORD record
ord-46a2b8ed5d124bc4a96ecd80a3508127
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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