Anisole → HCID 20545919, compound

HRID 2059309Notes

Reaction equation

[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21]CC)=[O:20])=[CH:12][CH:11]=1.[OH-].[K+]>>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][CH:3]=2)[CH2:17][C:18]([CH3:25])([CH3:24])[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=1

Participants

Reactant 3

HCID 7519Anisole

HCID 14797Potassium Hydroxide

HCID 54397833Ethyl 4-(4-chlorophenyl)-2,2-dimethylbut-3-enoate

Product 1

HCID 20545919HCID 20545919, compound

Procedure

Following the method of Rudenko et al*, anisole was alkylated with ethyl 4-(4-chlorophenyl)-2,2-dimethylbut-3-enoate. Hydrolysis of the ester with potassium hydroxide gave 4-(4-chlorophenyl)-4-(4-methoxyphenyl)-2,2-dimethylbutanoic acid, purified by washing with sodium bicarbonate solution and water. Recrystallization from ethyl acetate-light petrol (b.p. 60°-80°) afforded the acid as white prisms, m.p. 139°-142° (63%).

Sources & evidence

ORD record: ord-6813e334ce1e43d2b2d32dc223ad4161
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04322370

Reaction notes

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